GB877905A - Improvements in or relating to phosphoric acid ester derivatives of hydroxyalkyl or hydroxycycloalkyl esters of ª-,ª--ethylenically unsaturated monocarboxylic acids - Google Patents
Improvements in or relating to phosphoric acid ester derivatives of hydroxyalkyl or hydroxycycloalkyl esters of ª-,ª--ethylenically unsaturated monocarboxylic acidsInfo
- Publication number
- GB877905A GB877905A GB9558/58A GB955858A GB877905A GB 877905 A GB877905 A GB 877905A GB 9558/58 A GB9558/58 A GB 9558/58A GB 955858 A GB955858 A GB 955858A GB 877905 A GB877905 A GB 877905A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methacrylate
- group
- halogen
- chlorine
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 title 1
- 150000002763 monocarboxylic acids Chemical class 0.000 title 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 5
- 229910052801 chlorine Inorganic materials 0.000 abstract 5
- 239000000460 chlorine Chemical group 0.000 abstract 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 4
- 150000002367 halogens Chemical group 0.000 abstract 4
- 150000002430 hydrocarbons Chemical group 0.000 abstract 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052794 bromium Inorganic materials 0.000 abstract 3
- 229920001897 terpolymer Polymers 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract 2
- AOUSBQVEVZBMNI-UHFFFAOYSA-N 2-bromoethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCBr AOUSBQVEVZBMNI-UHFFFAOYSA-N 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000003063 flame retardant Substances 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 2
- 239000012433 hydrogen halide Substances 0.000 abstract 2
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 abstract 1
- -1 azo compound Chemical class 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000002657 fibrous material Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920001225 polyester resin Polymers 0.000 abstract 1
- 239000004645 polyester resin Substances 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000007870 radical polymerization initiator Substances 0.000 abstract 1
- 150000008028 secondary esters Chemical class 0.000 abstract 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
- D06M15/3564—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/117—Esters of phosphoric acids with cycloaliphatic alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F30/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F30/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention comprises polymers containing units of the formula: <FORM:0877905/IV (a)/1> wherein R is hydrogen, chlorine or a methyl group, R1 and R2 each represent a C1-C4 alkyl group or a C1-C4 halogen-substituted alkyl group in which each halogen substituent is chlorine or bromine and is attached to a carbon atom other than one bonded directly to oxygen, and A is a divalent saturated aliphatic or cycloaliphatic hydrocarbon group, said hydrocarbon group containing not more than 6 carbon atoms and providing a chain of at least two carbon atoms between the two adjacent oxygen atoms. The polymers may be obtained by polymerizing under the influence of a free-radical polymerization initiator such as a peroxide or azo compound, a monomeric compound of the formula: <FORM:0877905/IV (a)/2> wherein A, R, R1 and R2 are as defined above, (see Group IV(b)) either alone or with one or more other copolymerizable ethylenically unsaturated compounds, particularly those containing a <FORM:0877905/IV (a)/3> group, e.g. esters of acrylic or methacrylic acid or methacrylic acid itself. Examples are given for the production of (1) a copolymer of dimethylphosphatoethyl methacrylate and methyl methacrylate; (2) a terpolymer of diethylphosphatoethyl methacrylate, methyl methacrylate and methacrylic acid; (3) a terpolymer of diethyl phosphatoethyl methacrylate, methyl methacrylate and bromoethyl methacrylate; (4) a polyester resin compound obtained by heating a mixture of diethylphosphatoethyl methacrylate, bromoethyl methacrylate, styrene, and a solution of a polyester (derived from maleic and phthalic anhydrides and propylene glycol) in methyl methacrylate in the presence of benzoyl peroxide dispersed in tricresyl phosphate; and (5) a terpolymer of diethylphosphatoethyl acrylate, methyl methacrylate and methacrylic acid. The products have flame-retardant properties and can be used to impart such properties to textile and other fibrous materials, e.g. leather. Specification 595,881 is referred to.ALSO:The invention comprises compounds of the general formula <FORM:0877905/IV (b)/1> in which R is hydrogen, chlorine or a methyl group, R1 and R2 each represent a C1-C4 alkyl group or a C1-C4 halogen-substituted alkyl group in which each halogen substituent is chlorine or bromine and is attached to a carbon atom other than one bonded directly to oxygen, and A is a divalent saturated aliphatic or cycloaliphatic hydrocarbon group, said hydrocarbon group containing not more than six carbon atoms and providing a chain of at least two carbon atoms between the two adjacent oxygen atoms. They may be obtained by reacting together a hydroxy compound CH2=C(R)-CO.O.A.OH with a compound of the formula Q.P(O)(OR1)(OR2) wherein Q is a halogen atom other than fluorine or is an OR1 group. When Q is halogen other than fluorine the reaction is preferably carried out in the presence of a hydrogen halide acceptor and an inert solvent may be present. In an alternative procedure the hydroxy compound is reacted with a secondary ester of phosphorous acid of the formula HP(O)(OR1)(OR2) in the presence of an aliphatic polyhalide in which the halogen is chlorine, bromine or iodine e.g. carbon tetrachloride or tetrabromide or bromotrichloromethane the reaction being preferably effected in the presence of a hydrogen halide acceptor, e.g. a tertiary amine. Examples are given for the production of diethylphosphatoethyl acrylate and methacrylate, diethyl (and dimethyl) phosphatopropyl methacrylates and dimethyl phosphatoethyl methacrylate. The products can be polymerized either alone or with one or more copolymerizable compounds to yield products having good flame-retardant properties (see Group IV(a)). Specification 595,881 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US877905XA | 1957-03-29 | 1957-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB877905A true GB877905A (en) | 1961-09-20 |
Family
ID=22207281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9558/58A Expired GB877905A (en) | 1957-03-29 | 1958-03-25 | Improvements in or relating to phosphoric acid ester derivatives of hydroxyalkyl or hydroxycycloalkyl esters of ª-,ª--ethylenically unsaturated monocarboxylic acids |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1100287B (en) |
| FR (1) | FR1202964A (en) |
| GB (1) | GB877905A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969440A (en) * | 1974-09-23 | 1976-07-13 | Scott Paper Company | Phosphorus containing acrylic esters and amides |
| FR2536758A1 (en) * | 1982-11-30 | 1984-06-01 | Coatex Sa | NON-POLLUTANT FLUIDIFYING ADJUVANT FOR SALTWATER AND / OR FRESHWATER WATER-BASED DRILLING SLUDGE |
| US4612384A (en) * | 1981-07-29 | 1986-09-16 | Kuraray Co., Ltd. | Phosphate monoester adhesive composition |
| US5300604A (en) * | 1992-01-21 | 1994-04-05 | Naesman Jan Anders H | Process for making a macroporous styrene polymer |
| US5444123A (en) * | 1991-09-06 | 1995-08-22 | Basf Aktiengesellschaft | Halogen-free flameproofed thermoplastic molding materials based on polyphenylene ethers and polystyrene |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3346545A (en) * | 1964-10-30 | 1967-10-10 | Goodrich Co B F | Olefinically unsaturated phosphate and phosphonate monomers and process for making same and polymers therefrom |
| DE3623068A1 (en) * | 1985-07-12 | 1987-01-22 | Kao Corp | POLYMERS AND COPOLYMERS CONTAINING A PHOSPHATE GROUP AND PROCESS FOR THEIR MANUFACTURING |
| GB8812810D0 (en) * | 1988-05-28 | 1988-06-29 | Wiggins Teape Group Ltd | Radiation curable oligomers |
-
1958
- 1958-03-08 DE DER22864A patent/DE1100287B/en active Pending
- 1958-03-20 FR FR1202964D patent/FR1202964A/en not_active Expired
- 1958-03-25 GB GB9558/58A patent/GB877905A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969440A (en) * | 1974-09-23 | 1976-07-13 | Scott Paper Company | Phosphorus containing acrylic esters and amides |
| US4612384A (en) * | 1981-07-29 | 1986-09-16 | Kuraray Co., Ltd. | Phosphate monoester adhesive composition |
| FR2536758A1 (en) * | 1982-11-30 | 1984-06-01 | Coatex Sa | NON-POLLUTANT FLUIDIFYING ADJUVANT FOR SALTWATER AND / OR FRESHWATER WATER-BASED DRILLING SLUDGE |
| US5444123A (en) * | 1991-09-06 | 1995-08-22 | Basf Aktiengesellschaft | Halogen-free flameproofed thermoplastic molding materials based on polyphenylene ethers and polystyrene |
| US5300604A (en) * | 1992-01-21 | 1994-04-05 | Naesman Jan Anders H | Process for making a macroporous styrene polymer |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1100287B (en) | 1961-02-23 |
| FR1202964A (en) | 1960-01-14 |
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